HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$43+ Cheap flights from Pennsylvania to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
PHL — CHI
Feb 27 — Mar 61
Thu 2/27
Thu 3/6
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Pennsylvania to Chicago with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Pennsylvania to Chicago

Keep the following information in mind while searching for Pennsylvania to Chicago flight deals. Data was last updated February 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$89
(FlightHub)

One-way from

$43
(Cheapflightsfares)

Popular in

February

Cheapest in

September

Average price

$332

Good round-trip deal

$304 or less

Good one-way deal

$192 or less
Provider with most accurate pricing for Philadelphia-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Philadelphia-Chicago (CHI) flights.
Search Deals
From Pennsylvania to Chicago (CHI)
Search Deals
One-way flight from Pennsylvania to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 29% potential increase in price ($86 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2025
Search Deals
Price to beat on a round-trip flight from Pennsylvania to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Pennsylvania to Chicago (CHI).
Search Deals

Find flight deals from Pennsylvania to Chicago

Cheapest flights from Pennsylvania to Chicago
Explore the most affordable flight options available from Pennsylvania to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 22, 2025.

This FlightHub deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/169:33 pmEWR - ORD
Nonstop2h 37mSpirit Airlines
Mon 5/195:10 pmORD - EWR
Nonstop2h 18mSpirit Airlines
Deal found 2/21$89
This Cheapflightsfares deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1110:58 amLGA - ORD
1 stop13h 58mSpirit Airlines
Thu 3/1312:31 pmORD - LGA
Nonstop2h 04mSpirit Airlines
Deal found 2/21$95
This Cheapflightsfares deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/2511:01 amJFK - MDW
1 stop5h 52mFrontier
Tue 4/14:40 pmMDW - JFK
1 stop7h 03mFrontier
Deal found 2/21$98
This Justfly.com deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/76:00 amEWR - ORD
Nonstop2h 44mMultiple Airlines
Sat 3/82:25 pmORD - EWR
1 stop5h 44mMultiple Airlines
Deal found 2/21$99
This Mytrip deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/181:01 pmJFK - ORD
1 stop21h 04mFrontier
Tue 4/19:22 amORD - JFK
1 stop23h 38mFrontier
Deal found 2/20$100
This Kiwi.com deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/15:30 pmLGA - ORD
1 stop6h 41mMultiple Airlines
Mon 5/55:55 amORD - LGA
Nonstop2h 05mMultiple Airlines
Deal found 2/21$100
This Frontier deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/510:00 pmLGA - MDW
1 stop14h 31mFrontier
Tue 3/117:50 amMDW - LGA
1 stop12h 09mFrontier
Deal found 2/21$100
This Frontier deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1210:00 pmEWR - MDW
1 stop11h 19mFrontier
Sat 5/1710:48 amMDW - EWR
1 stop9h 18mFrontier
Deal found 2/21$104
This Frontier deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/310:00 pmLGA - ORD
1 stop12h 51mFrontier
Tue 3/42:25 pmORD - LGA
1 stop7h 35mFrontier
Deal found 2/22$117
This Frontier deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/2510:10 pmEWR - ORD
1 stop10h 18mFrontier
Wed 3/59:08 amORD - EWR
1 stop11h 02mFrontier
Deal found 2/21$123
This KAYAK deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/288:00 amJFK - ORD
Nonstop2h 55mDelta
Wed 4/307:20 amORD - JFK
Nonstop2h 19mDelta
Deal found 2/21$145
This JetBlue Airways deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/110:35 amJFK - ORD
Nonstop2h 42mJetBlue
Sun 5/46:20 amORD - JFK
Nonstop2h 13mJetBlue
Deal found 2/22$147

Find flights from Pennsylvania to Chicago within your budget

Customize your flight search to find flights from Pennsylvania to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 22, 2025.

Fly from

Pennsylvania

Fly to

Chicago

Route

Depart

Return

Price

NewarkChicago

EWR - ORD

EWRORD

Newark

Fri 5/16

9:33 pm-11:10 pm

Nonstop2h 37m

Chicago O'Hare Intl

Sun 5/18

5:10 pm-8:28 pm

Nonstop2h 18m

$89

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 3/11

10:58 am-11:56 pm

1 stop13h 58m

Chicago O'Hare Intl

Thu 3/13

12:31 pm-3:35 pm

Nonstop2h 04m

$95

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Tue 3/25

11:01 am-3:53 pm

1 stop5h 52m

Chicago Midway

Tue 4/1

4:40 pm-12:43 am

1 stop7h 03m

$98

NewarkChicago

EWR - ORD

EWRORD

Newark

Fri 3/7

6:00 am-7:44 am

Nonstop2h 44m

Chicago O'Hare Intl

Sat 3/8

2:25 pm-9:09 pm

1 stop5h 44m

$99

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Tue 3/18

1:01 pm-9:05 am

1 stop21h 04m

Chicago O'Hare Intl

Tue 4/1

9:22 am-10:00 am

1 stop23h 38m

$100

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 5/1

5:30 pm-11:11 pm

1 stop6h 41m

Chicago O'Hare Intl

Mon 5/5

5:55 am-9:00 am

Nonstop2h 05m

$100

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 3/5

10:00 pm-11:31 am

1 stop14h 31m

Chicago Midway

Tue 3/11

7:50 am-8:59 pm

1 stop12h 09m

$100

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 4/1

10:00 pm-10:40 am

1 stop13h 40m

Chicago O'Hare Intl

Sat 4/5

7:20 am-10:32 am

1 stop26h 12m

$103

NewarkChicago

EWR - MDW

EWRMDW

Newark

Mon 5/12

10:00 pm-8:19 am

1 stop11h 19m

Chicago Midway

Sat 5/17

10:48 am-9:06 pm

1 stop9h 18m

$104

NewarkChicago

EWR - ORD

EWRORD

Newark

Tue 2/25

10:10 pm-7:28 am

1 stop10h 18m

Chicago O'Hare Intl

Wed 3/5

9:08 am-9:10 pm

1 stop11h 02m

$123

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/22

Showing 1-10 of 60 results
1
2
3
...
6

Best time to book a flight from Pennsylvania to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Pennsylvania with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Pennsylvania to Chicago

Get recent, data-driven insights about flights from Pennsylvania to Chicago including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Pennsylvania to Chicago?

Currently, August is the cheapest month in which you can book a flight from Pennsylvania to Chicago (average of $245). Flying from Pennsylvania to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from PA to CHI?

Find hourly flight availability from Pennsylvania to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 22, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Pennsylvania to Chicago as you normally would.

Weekly flight availability from Pennsylvania to Chicago

Explore weekly flight availability from Pennsylvania to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated February 22, 2025.

The most flights from USPA to CHI are scheduled on a Thursday (41 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (25 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated February 22, 2025.
To help decide which airline to fly from Pennsylvania to Chicago, see what other customers have to say about Southwest, Alaska Airlines and Delta. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,395 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,395 reviews
Southwest
8.1
Very good
4,395 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,700 reviews
Southwest
8.1
Very good
4,395 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,203 reviews
Southwest
8.1
Very good
4,395 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,068 reviews
Southwest
8.1
Very good
4,395 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,754 reviews
Southwest
8.1
Very good
4,395 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

Find useful and relevant information for your journey from Pennsylvania to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Pennsylvania to Chicago one-way?

    $43 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on Frontier and Delta, with prices starting from $51 and $74, respectively.

  • What are the most popular routes from Pennsylvania to Chicago?

    When deciding which route to take from Pennsylvania to Chicago consider New York John F Kennedy Intl - Chicago O'Hare Intl, Newark - Chicago O'Hare Intl or New York LaGuardia - Chicago O'Hare Intl as they are the most popular.

  • What are the most reliable airlines from Pennsylvania to Chicago?

    No one likes to see their flight delayed. When booking a flight from Pennsylvania to Chicago consider choosing SWISS (100%), Spirit Airlines (100%) or Copa Airlines (97%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Pennsylvania to Chicago?

    On average you can expect to pay $1,016 for a flight from Pennsylvania to Chicago. The cheapest flight overall is $109 while the most popular route, (New York John F Kennedy Intl - Chicago O'Hare Intl) is currently priced at $83.

  • Can I find deals for flights from Pennsylvania to Chicago that include hotel bookings?

    Yes. In addition to deals on Pennsylvania to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Pennsylvania to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Pennsylvania to Chicago.

  • Can I find deals for business class flights from Pennsylvania to Chicago?

    Yes. Cheapflights offers flight deals from Pennsylvania to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Pennsylvania to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Pennsylvania to Chicago (average of $245). Flying from Pennsylvania to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Pennsylvania?

Book flights to Pennsylvania if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Pennsylvania to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Newark to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
Boston to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Seattle to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Denver to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Newark to Midway flights
Philadelphia to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Ontario to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Los Angeles to Midway flights
Sky Harbor Intl to O'Hare Intl flights
Hobby to O'Hare Intl flights
Burbank to O'Hare Intl flights
LaGuardia to Midway flights
Austin to O'Hare Intl flights
San Diego to O'Hare Intl flights
Dulles Intl to Midway flights
Orlando to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Seattle to Midway flights
Charlotte to O'Hare Intl flights
Atlanta to Midway flights
Dallas/Fort Worth to Midway flights
Hobby to Midway flights
Tampa to O'Hare Intl flights
San Francisco to Midway flights
Newark to St. Louis flights
Miami to O'Hare Intl flights
Love Field to O'Hare Intl flights
Hartford to O'Hare Intl flights
Portland to O'Hare Intl flights
Minneapolis to Midway flights
LaGuardia to St. Louis flights
Baltimore to Midway flights
Boston to Midway flights
Cleveland to O'Hare Intl flights
Detroit to O'Hare Intl flights
Reagan-National to Midway flights

Top 5 airlines flying from Pennsylvania to Chicago

Discover the top 5 airlines that operate flights from Pennsylvania to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$48Average$122FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$127Average$331FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$136Average$350FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$152Average$291FlexibilityNo cancel feeOn-time63%
DeltaCheapest$155Average$362FlexibilityNo cancel feeOn-timeN/A
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.